Iva-Val | 39741-06-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Iva-Val
• 英文别名: N-isovaleryl-L-valine；N-Isovaleryl-L-valin；L-Valine, N-(3-methyl-1-oxobutyl)-；(2S)-3-methyl-2-(3-methylbutanoylamino)butanoic acid
• CAS: 39741-06-5
• 化学式: C₁₀H₁₉NO₃
• 分子量: 201.266
• InChiKey: OPJHQXJQYXRMGN-VIFPVBQESA-N

物化性质

• 沸点：
  381.8±25.0 °C(Predicted)
• 密度：
  1.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Iva-Val 在 sodium hydroxide 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 生成 Iva-Val-D-Val-OH
  参考文献：
  名称：

  Affinity chromatography of pepsin using pepstatin fragments as ligands of specific sorbents

  摘要：

  DOI：

  10.1007/bf00573554
• 作为产物：
  描述：

  异戊酸 、 L-缬氨酸 在 adenosine monophosphate ligase SfaB from Streptomyces thioluteus 、 5’-三磷酸腺苷 、 magnesium chloride 、 Cleland's reagent 作用下， 以 aq. buffer 为溶剂， 反应 6.0h， 生成 Iva-Val
  参考文献：
  名称：

  重新利用3-异氰基丁酸腺苷酸化酶SfaB进行多功能酰胺化和硫酯化

  摘要：

  微生物天然产物的基因组挖掘使化学家不仅能够发现具有新颖骨架的生物活性分子，而且能够识别催化多种化学反应的酶。探索这些生物合成酶的底物混杂性和催化机理有助于开发潜在的生物催化剂。SfaB是一种形成酰基腺苷酸的酶，可在由硫链霉菌产生的二异腈自然产物SF2768的生物合成途径中，对独特的结构单元3-异氰基丁酸进行腺苷酸化。，并且该AMP连接酶被证明可以接受各种短链脂肪酸（SCFA）。在本文中，我们将SfaB重新用于催化那些SCFA与各种胺或硫醇亲核试剂之间的酰胺化或硫酯化反应，从而提供了另一种酶促方法来体外制备相应的酰胺和硫酯。

  DOI：

  10.1002/anie.202010042

文献信息

• Analysis of Cigarette Mainstream Smoke for 1,1-Dimethylhydrazine and Vinyl Acetate by Gas Chromatography-Mass Spectrometry
  作者：J. Diekmann、C. Biefel、K. Rustemeier

  DOI：10.1093/chromsci/40.9.509

  日期：2002.10.1

  1,1-Dimethylhydrazine, also known as unsymdimethylhydrazine (UDMH) and vinyl acetate (VA), are both classified by the International Agency for Research on Cancer as 2B carcinogens (possibly carcinogenic to humans) and listed as cigarette smoke constituents; however, there is little or no quantitative data available on them. For UDMH in cigarette smoke, neither a yield nor a method has been published. For VA, the most recent information on yields dates back to 1965. To bridge this gap, we have developed new gas chromatographic-mass spectrometric methods for both compounds to determine their yields in cigarette smoke. UDMH is determined by derivatization with 2-nitrobenzaldehyde in methanol and is not found in cigarette smoke at levels above the detection limit of 19 ng/cig. In further experiments, when UDMH is added to the smoke stream or air stream of lit or unlit cigarettes, the derivative 2-nitrobenzaldehyde-2,2-dimethylhydrazone is found only in the air stream of the unlit cigarettes. From this, we conclude that UDMH is either not formed during smoking at all or, if it is, it reacts immediately and quantitatively with other smoke constituents (e.g., aldehydes) and is therefore not detectable in cigarette smoke. VA is determined by trapping in acetone at −78°C and is found at a concentration of 270 ng/cig for a standard reference cigarette with a cellulose acetate filter (the reference cigarette 1R4F). In the literature, VA is reported at concentrations of 1.6 µg/cig for a cigarette with a cellulose acetate/charcoal filter and 4 µg/cig for a cigarette with a cellulose acetate filter and for an unfiltered cigarette.

  1,1-二甲基肼，又称未二甲基肼（UDMH）和醋酸乙烯酯（VA），均被国际癌症研究机构列为 2B 级致癌物（可能对人类致癌），并被列为香烟烟雾成分；然而，有关它们的定量数据却很少或根本没有。对于香烟烟雾中的 UDMH，既没有公布产量，也没有公布方法。至于 VA，最新的产量信息可追溯到 1965 年。为了弥补这一差距，我们针对这两种化合物开发了新的气相色谱-质谱分析方法，以确定它们在香烟烟雾中的产量。UDMH 是通过甲醇中的 2-硝基苯甲醛衍生化来测定的，其在香烟烟雾中的含量不会超过 19 纳克/支的检测限。在进一步的实验中，当将 UDMH 加入点燃或未点燃的香烟的烟流或气流中时，只在未点燃香烟的气流中发现衍生物 2-硝基苯甲醛-2,2-二甲基腙。由此，我们得出结论：UDMH 要么根本不会在吸烟过程中形成，要么即使形成了，也会立即与其他烟雾成分（如醛类）发生定量反应，因此无法在香烟烟雾中检测到。VA 在-78°C 的丙酮中进行捕集测定，在带有醋酸纤维素过滤嘴的标准参考香烟（参考香烟 1R4F）中，VA 的浓度为 270 纳克/支。据文献报道，醋酸纤维素/木炭过滤嘴香烟的 VA 浓度为 1.6 微克/千克，醋酸纤维素过滤嘴香烟和未过滤香烟的 VA 浓度为 4 微克/千克。
• [EN] PHOSPHONAMIDATE ESTER-CONTAINING PSEUDOPEPTIDES
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：WO1993009134A1

  公开（公告）日：1993-05-13

  (EN) A 'capped' phosphonamide C1-C6 alkyl ester linkage unit for joining peptides is disclosed. The linkage unit is substantially isosteric and isocoulombic as compared to conventional peptide backbone structures. The 'capping' of the phosphonamide by the C1-C6 alkyl ester causes the linkage unit to be acid stable. When incorporated into a peptide, the phosphonamide C1-C6 alkyl ester linkage unit becomes resistant to cleavage by aspartic proteinase. Accordingly, the phosphonamide C1-C6 alkyl ester linkage unit enhances and/or facilitates the aspartic proteinase inhibition activity of peptides into which it is incorporated.(FR) Une unité 'coiffée' de liaison à ester d'alkyle C1-C6 de phosphonamide est utile pour relier des peptides. L'unité de liaison est essentiellement isotérique et isocoulombienne par rapport aux squelettes peptidiques classiques. Le fait que le phosphonamide est 'coiffé' par l'ester d'alkyle C1-C6 rend l'unité de liaison stable aux acides. Lorsqu'elle est incorporée à un peptide, l'unité de liaison à ester d'alkyle C1-C6 de phosphonamide devient résistante au clivage par la protéinase aspartique. Par conséquent, l'unité de liaison à ester d'alkyle C1-C6 de phosphonamide améliore et/ou facilite l'activité d'inhibition de la protéinase aspartique des peptides auxquels elle est incorporée.

  一种连接肽的磷酸酰胺加成C1-C6甲基酯连接单元被揭示了。与传统肽骨架结构相比，该连接单元在等离子体和电荷方面是等离子体和电荷稳定的。磷酸酰胺的C1-C6甲基酯封口使连接单元呈现酸稳定特性。该连接单元被整合到肽中时，会使磷酸酰胺C1-C6甲基酯连接单元具有抵御蛋白酶box.slice增强的能力。因此，磷酸酰胺C1-C6甲基酯连接单元增强或促进整合到其中的肽的蛋白酶抑制活性。
• Simplified Pepstatins:  Synthesis and Evaluation of N-Terminally Modified Analogues
  作者：Martin Kratzel、Birgit Schlichtner、Roland Kirchmayer、Andreas Bernkop-Schnürch

  DOI：10.1021/jm9807306

  日期：1999.6.1

  The promising strategy of gastric ulcer healing with perorally administered epidermal growth factor (EGF) is so far strongly limited by the pepsinic degradation of this therapeutic polypeptide in the stomach. The incorporation of EGF in a bioadhesive polymer-pepsin inhibitor conjugate used as drug carrier matrix, however, might provide sufficient protection toward pepsinic degradation. The synthesis of appropriate pepsin inhibitors represents a prerequisite for the development of such polymer-inhibitor conjugates. The presented study demonstrates that modifications at the N-terminus of simplified analogues of pepstatin which can be synthesized in a simple and straight way result only in slight variations of the inhibitory activity. These analogues display only 10-fold reduced-inhibitory activity, compared to pepstatin A, when bearing a greater N-terminal group like isovaleryl, Boc, or Cbz. Compounds which are substituted at the N-terminus by a shorter N-acyl group like propionyl or cyclopropylcarbonyl show further reduced activity (0.01, compared to pepstatin A). The presence of an amide or a urethane moiety at the N-terminus has no considerable effect on enzyme inhibition. Therefore, the N-terminus of these analogues is able to be modified forming a covalent bond to various bioadhesive polymers via a suitable functionality.
• Potent inhibition of pepsin and penicillopepsin by phosphorus-containing peptide analogs
  作者：Paul A. Bartlett、John E. Hanson、Peter P. Giannousis

  DOI：10.1021/jo00313a012

  日期：1990.12

  Phosphinic and phosphonic acid peptide derivatives have been evaluated as inhibitors of the aspartic proteases pepsin and penicillopepsin. The most potent of those studied is isovaleryl-Val-Val-Leu(P)-(O)Phe-Ala-Ala-OMe (4) (Leu(P) represents the phosphonic acid analogue of leucine; (O)Phe represents L-beta-phenyllactic acid, the alcohol analogue of phenylalanine), for which the K(i) values for pepsin and penicillopepsin are 0.26 and 0.19 nM, respectively. While this compound binds to penicillopepsin with an association rate constant, k(on), of (6.5 +/- 1.5) X 10(5) M(-1) s(-1), it does not show slow- or two-step binding with pepsin. The binding of Cbz-Ala-Ala-Leu(P)-(O)Phe-OMe (1) to penicillopepsin is strongly dependent on pH: in comparison to pH 4.5, the affinity at pH 3.5 is increased 10-fold and at pH 5.5 it is decreased 40-fold. The two diastereomers of a nonionic phosphinamide analogue (10A, 10B) of a statine-containing inhibitor were prepared; however, both are significantly weaker inhibitors of pepsin than the phosphinic acid itself (7).
• MERRELL, DOW;SCHIRLIN, DANIEL;PELTON, JOHN TOM;TARNUS, CELINE;JUNG, MICHE+
  作者：MERRELL, DOW、SCHIRLIN, DANIEL、PELTON, JOHN TOM、TARNUS, CELINE、JUNG, MICHE+

  DOI：——

  日期：——